Triphenylphosphine → 2-(3-Bromophenylthio)-3-[3-(pyridin-3-yl)propoxy]pyridine

3-(Pyridin-3-yl)-1-propanol (5.5 g, 40 mmol) and triphenylphosphine (10.5 g, 40 mmol) are dissolved in THF (120 ml), and thereto are added successively with stirring diisopropyl azodicarboxylate (6.1 g, 30 mmol) and 2-(3-bromophenylthio)-3-pyridinol (5.0 g, 18 mmol) obtained in Reference Example 1 under ice-cooling. The mixture is further stirred at room temperature for 30 minutes, and the reaction solution is concentrated under reduced pressure. To the residue is added ethyl acetate (300 ml), and the mixture is extracted with a 10% aqueous hydrochloric acid solution (150 ml×2). The pH value of the aqueous layer is adjusted to pH 12 with potassium carbonate, and the mixture is extracted with ethyl acetate (200 ml×2). The organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane), and recrystallized from diethyl ether to give the title compound (6.8 g) as colorless crystals, m.p. 75-76° C.

1. customobtained in Reference Example 1 under ice-
2. temperaturecooling
3. concentrationthe reaction solution is concentrated under reduced pressure
4. additionTo the residue is added ethyl acetate (300 ml)
5. extractionthe mixture is extracted with a 10% aqueous hydrochloric acid solution (150 ml×2)
6. extractionthe mixture is extracted with ethyl acetate (200 ml×2)
7. washThe organic layer is washed with a saturated brine (50 ml×2)
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)
11. customrecrystallized from diethyl ether

ORD-Eintrag

ord-97fbb43e9c9c49b1ba0dafc44fe899fd

Quelldatensatz

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06765095B2